


Big brother knows best

by Winmance



Category: Supernatural
Genre: Break Up, Fanart, First Dates, First Kiss, Fluff, Gay Sam Winchester, M/M, Pre-Season/Series 01, Supportive Dean Winchester
Language: English
Status: Completed
Published: 2019-02-14
Updated: 2019-02-14
Packaged: 2019-10-28 04:54:06
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,677
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17780948
Author URL: https://archiveofourown.org/users/Winmance/pseuds/Winmance
Summary: Sam's boyfriend dumped him, and if it wasn't bad enough, he chose Valentine's day to do it.Luckily for him, his brother is here to cheer him up.





	Big brother knows best

**Author's Note:**

> Beta by debivc78

Dean parked the car in front of the motel, opening the door with one hand while grabbing the beer next to him with the other. He hopes it's enough to get him drunk to the point where he can’t remember who he is or where he is. Maybe then he'll watch the porn he bought a few towns away, or maybe simply channel surf until he finds something decent on tv to watch. He’s not sure yet, but either way, tonight’s gonna be a, boring night.

Reaching back inside the car, Dean picks up a small grocery bag and stares at it for a moment.  Shaking his head, he slams the car door a little too hard and heads inside.

“Heya Sammy” He says, throwing the grocery bag on Sam’s bed “Got you something for tonight”

He turns toward the fridge, trying to hide the smirk on his face. To be fair, he did buy the contents of the bag for Sam, but he knows for a fact that his brother’s gonna be embarrassed as fuck and well, he’s only human after all.

But when he takes a look at Sam, his smile dies. Instead of a dark blush on Sam’s cheeks and an embarrassed look on his pretty face, Sam’s expression is as closed as ever, no emotion.

“You ok?” Dean frowns, ready for the worst. There are only a few things that would make Sam this sad and angry.

One is if he got a bad grade, which Dean knows didn’t happen because otherwise, he would already have heard about it.

Another is if their dad had called and told them that they were leaving. But that doesn’t make any sense either because Dad said he wouldn’t be back for at least another two weeks.

And finally, if someone had been mean to him.

“Did someone hurt you?”

“No” Sam says, without lifting his head from his book

“What’s up with the bitch face then? You don’t like my gift?”

“I won’t need it. You can take it back”

“Well, I rather you take it” He says, dropping on his own bed next to Sam, “I know what happens on Valentine day”

“Nothing will happen”

“Yeah, of course. I’m sure your boyfriend, who can’t seem to be able to put his hands away from your ass more than a few seconds, doesn’t have anything remotely sexual planned tonight” He laughs, ignoring the way his stomach flipped. “Take the lube and condoms, already. You might need them”

“I won’t”

“Well, your boyfriend-“

“I don’t have one anymore” Sam snaps, his voice breaking at the end of his sentence

Dean’s heart missed a beat, and he pushed himself up right away, moving toward Sam.

“What happened?”

“Josh dumped me” Sam whispers, still not meeting Dean’s eyes

“When?”

“During lunch. He said he realized that we weren’t mean to be, whatever the fuck it means”

“That little fucker” Dean says, clenching his jaw.

He can’t think of one single reason of why someone would dump Sam, much less on Valentine’s day. Couldn’t he have done it before? So Sam wouldn’t spend the rest of his life thinking of it as the day his heart got broken?

Or he could've done it after. So they could spend one good day together before ending things? No, Dean pushed that idea from his mind quickly.  If he'd have done it after, they might have had sex and then it would have forever been the day Sam lost his virginity only to have the bastard who took it, break his heart the next day.

“Yeah” Sam simply answers quietly

Dean's mood softens as he sees Sam’s face. He looks so small, so young, the fifteen year old teenager completely disappearing. He looks the way he did when Dad left them at Bobby’s house one day before his fifth birthday, even though he promised Sam he would be there to celebrate it with him. Dean can remember all too well the vivid pain he felt, seeing his brother so hurt.

He got up from his bed and sat next to Sam, pulling him into his arms.

Sam breaks down.  Hot tears running down his face, he clung to Dean as if he were holding on to life itself.

“I’m here Sammy, it’s gonna be alright” Dean whispered, rocking him slowly.

“What is wrong with me, Dean?” Sam sobs, “What do I keep doing wrong?”

“Nothing, Sam, nothing. You’re not doing anything wrong, you’re perfect”

“No, I’m not! No one wants to stay with me. Not Josh, not dad, not even you. I keep- I keep pushing everyone away, and I don’t know- I don’t know why. Why am I like that? What's wrong with me?” His voice breaks as he whispers again, even lower this time, “What's wrong with me?”

Dean doesn’t answer, knowing too well that whatever he'd say right now would go over Sam’s head. He doesn’t trust his voice to speak out loud  anyway. How can Sam think that? How can Sam think that something is wrong with him, when he’s nothing but perfect. From his weird little toes to the one white hair that keeps growing on his head. What did Dean do so wrong that Sam thinks he doesn’t want to stay with him?

He holds Sam until he falls asleep, too tired from crying to keep his eyes open.

There goes his boring night.

 

 

 

Sam opens his eyes slowly, his mind a little dizzy as he tries to remember what happened earlier. He remembers falling asleep against Dean, so he starts looking for him right away.

The room is completely empty, not that Sam is surprised. Why would Dean stay? It’s Valentine’s day, and even his own boyfriend didn’t want to be with him, why would Dean want to?

If he’s being honest, he doesn’t give two fucks about Josh. Sure, Josh was cool, he was a pretty good kisser, and Sam won’t deny that there was a physical attraction. But he couldn’t talk to Josh, he couldn’t tell him about monsters, about his dad, and Josh didn’t really get any of his jokes, he didn’t understand him without him having to say anything. Josh wasn’t Dean.

But he still doesn’t understand why Josh left him. He didn’t do anything wrong, not that he can think of. He wasn’t always begging for attention, even through he was dying for it, and he let Josh do whatever he wanted. He wasn’t a little prude, and they both experimented a little together – as much as they could with clothes on. They never fought, not once, and Sam was pretty sure everything was doing fine.

Of course it wasn’t. Because nothing ever goes fine with Sam, every last bit of happiness he experiences, goes away before he can ever start to embrace it.

He pushed himself out of the bed and walked toward the bathroom, dragging his body. Is this how it will always be? Him completely alone in a dark room, abandoned by every single person he ever loved? That’s not the life he wants. Not even close.

He hears the sound of keys in the door, followed by foot steps that he recognizes as Dean’s right away.

“Dean?” He frowns, sticking his head out of the bathroom, “What are you doing here?”

“Yeah, I, uh” Dean stutters, scratching his head with embarrassment, much to Sam surprise, “I thought maybe you could come with me”

“I can’t go to bar, I’m fifteen, remember?”

“I know that dickhead, I didn’t say anything about a bar!” Dean sighs in frustration, “Can you please come with me?”

“Where?”

“Just come!”

Sam rolls his eyes, ignoring his brother's frustration. He knows better than to argue, he can tell the difference between frustrated Dean and angry Dean.

He’s about to come out of the room when Dean’s throws a red sweatshirt at him, almost making him bang his head.

“Sorry” Dean says with a grimace, “But you’ll need that”

“Jeez Dean, relax a little”

He sighs, walking toward the car and sliding inside without waiting for Dean. There’s a couple in the doorway next to their room, so lost in their kiss that they don’t even notice Dean when he almost bumps into them, and Sam mentally curses himself for agreeing to go out.

He doesn’t know where they are going, but he knows that he’ll be reminded all night that everybody's got a boyfriend except him. What kind of douchbag gets dumped on Valentine’s Day? God, what he would give to make this day end already. He just wants to curl up in his bed and never goes out again.

“You good?” Dean asks, a concerned look on his face

“Yeah, just… Not sure I want to go out” He says, sliding down in the car seat.

“It’s gonna be fun, I promise” Dean winks at him before turning his head toward the backseat, “There’s something for you here”

Sam frowns but turns around, grabbing the plastic bag while Dean starts driving. He notices it's the same grocery bag from earlier, and catches a glimpse of the lube and condoms now laying on the floor of the car in the back.  He swears, if this is another sex toy like the one a month ago, he’s gonna smack Dean in his stupid head with it.

“Chocolates?” He frowns, holding the heart shaped box in his hands. "Why did you buy me chocolates? Is there laxative in them? Because that wasn’t funny, and Dad said it was dangerous”

“Ok, first of all, I’m not dumb, I looked it up before giving you the laxative. I couldn’t have known you’re body was so weak”

“You’re weak”

“Whatever” Dean continues, “There is no laxative in them. It’s just… A present.”

“For what?”

“For… You know”

“I don’t”

“Don’t make me say it”

“Well, I don’t- Oh” He says, realization hitting him. Valentine’s Day. Dean got him a present for Valentine’s Day. He feels his cheeks suddenly starting to burn, and he quickly turns his head, not wanting Dean to see him. “Thanks, Dean”

“It’s not weird, right?” Dean quickly asks

“No, I mean, Valentine’s day is about love, it doesn’t have to be romantic”

“Yeah, exactly”

“There’s a kid at school that spends Valentine's Day with his parents. They go to restaurant, theater, and even get each other presents”

“That’s… A little weird. Weirder than us”

“Exactly” Sam reassures him, looking at the heart shaped box in his hands, a smile on his face. Dean took the time to go back to the store just to buy it for him, and was even careful enough to get the one with only dark chocolate in it.

He looked at Dean from the corner of his eye, and he isn’t surprised to catch his brother doing the same, even though he quickly turns his stare back to the road.

Sometimes, he thinks Dean knows. That he somehow found out about Sam’s secret, and that it’s the reason why he acted so distant sometimes. But then if he had, he wouldn’t have gotten him a heart shaped box of chocolates, and he wouldn’t be taking him out for Valentine’s Day.

Dean’s turns the music louder when his favorite song comes on, and he starts singing before telling Sam to join him. 

“Come on Sammy, let it out!”

Sam shakes his head with a laugh before opening his mouth, letting the words go, melting with Dean’s own voice. It’s an incredible feeling, to be in the car with Dean singing out loud, and not caring about who's listening or watching.

He'd spent so long hating this car; cursing it for always driving them  from town to town, cursing it whenever he would see it waiting in the parking lot of his school, kicking it discreetly for being Dean’s favorite, for having the honor of being called “baby”, for taking so much time from Dean, so much precious time.

But he doesn’t hate it anymore. Not since he realized that every time it drove them to a new town, it allowed them to stay together. That every time he saw it waiting outside, it meant that Dad and Dean were alright. That every single second Dean spent working on it was to make sure it was safe for both of them. That every time Dean cleaned it was so they could go and buy their favorite ice cream before laying on top of the car, the space between them so small that their fingers touched.

He used to hate this car, but now he’s singing out loud with Dean, huge smiles on both of their faces as they get to the best part of the song, and he never felt closer to home.

“Here we go” Dean says, parking the car

“Is this…”

A funfair” Dean says, a huge smile on his face

“Fuck, I can’t believe you did this!” He throws his arms around Dean’s neck before his brother can even react, “Thank you!”

“Easy tiger” Dean laughs, his whole body vibrating with it, “Glad you like it”

“Like it? I've wanted to go for years! But dad always said they were too dangerous and useless”

“Yeah well, dad’s not here and I thought you deserved a little something” Dean gave him a smile, before ruffing his hair, opening his door, “Come on, we need to started now if we want to do everything!”

Sam got out of the car and ran next to Dean, letting his brother’s arm lay casually over his shoulders as he hurries him to walk.

They start with the haunted house, because according to Dean, it was the least interesting one. Surely, when you hunt monsters for a living, the fake monsters doesn’t look as scary as they should.

“There’s gonna be a huge spider right here” Dean announces as they walk in the house

“You’re killing all the fun” Sam complains, even though he’s been laughing for the last fifteen minutes already

“Oh, so it’s my fault if they can't think of anything better than plastic spiders?”

“No, but it’s-“ Sam cuts off his sentence with a scream, and Dean pushes Sam behind him out of instinct, ready to defend his brother.

In front of them was the most terrifying clown Sam's ever seen, with a skin so white that it makes his bloody eyes even scarier.

“It’s a dummy, Sam” Dean says once he checks the thing, “Nothing but a stuffed dummy”

“I’m scared” Sam admits, his heart pounding harder the more he looks at it.

“Ok, ok” Dean reassures him before holding his hand, “We just need to get through this one, and then that’s it. Can you do that?”

“Don’t let go, ok?”

“Never”

They start walking again, Sam holding Dean’s hand as tight as possible, passing just a few inches away from the dummy, who’s head turns as they do so.

“Almost done” Dean reassures him, pulling him to make him go faster, “Here we go”

Sam eyes don’t leave the terrifying figure, not until they're completely out of the house, and even then he doesn’t let go of Dean’s hand.

“I hate clowns” He complains, “Hate them so much”

“I know. I didn’t think there would be any”

“Couldn’t predict that one, could you?” Sam rags on him, his sense of humor coming back.

“Or maybe I just enjoy watching you suffer. Who knows?”

Sam rolls his eyes before shoving Dean, which earns him a shove out of the way. Luckily, he’s still holding Dean’s hand, keeping him from falling.

“Come on, let’s do the house of mirrors." Dean says, dragging him along.

Much to Sam’s disappointment, neither Dean nor him runs into a mirror, nor did they get lost in the labyrinth, but the fact that Dean still hasn’t let go of his hand through the whole thing makes up for the lack of fun.

“Wanna eat something before doing La Grande Roue” Dean says in a surprisingly decent French accent, a proud smile on his face

“Oh you speak French now?”

“Of course, mon amour” Dean says, sliding his arm around Sam’s waist to drag him closer to him and try to kiss him

Sam bursts into laughter as he tries to avoid Dean kissing him, which ends up with him almost falling on the ground. Luckily, Dean’s arm is there to catch him.

“Sometimes I feel like you’re still a toddler. If I let go of you for more than five seconds, boom, you’re on the ground”

“My body is really tall, ok?”

“Looks kind of small to me” Dean says with a grin

“I’ll be taller than you before you can ever realize it”

“I wouldn’t get my hopes to high if I was you” He laughs, ordering their food at the same time, “But that’s cool. Being small is cute”

“Better than being an ass. Which you are”

“Really funny”

Sam laughs, biting in his corndog and making sure to chew on it as loud as possible to annoy Dean. He doesn’t have time to react before Dean’s teeth are deep in his corndog, taking as much of it as he can.

“Hey! That’s mine!” He complains

“What is yours is mine, little bro” He ignores the way Sam rolls his eyes, dragging him toward another attraction. “Alright, which one do you want?”

It’s during times like this that Sam thanks whatever God is out there for having given him Dean as his big brother. If it had been anyone else, his or her brother would have blown off his or her post-break up pain like it was nothing, or simply ignored it. But not Dean. No, Dean bought him chocolates, took him to a funfair, and now, he’s asking Sam to choose which teddy bear he wants him to win for him.

He knows that Dean would have rather be out with some no name girl, kissing her and celebrating Valentine’s Day like he always does. But he chose to be with Sam instead, still choosing Sam’s happiness over his.

“Earth to Sam” Dean says, passing his hand in front of Sam’s face

“Sorry” He looks at all the teddy bears in front of them, and the numbers you have to shoot in order to win one. “I want the biggest”

“Of course you do”

Dean sighs, but Sam knows for sure that he’s more than happy to be able to show off his shooting skills.

He takes the gun, aims it, turns his head to wink at Sam, and purposely misses the first target.

“Really?” Sam says, “You’re supposed to impress me during our date. Otherwise I won’t put out”

Dean laughs, deep and loud, his head falling back as he does so, and not for the first time, Sam has to fight the urge to throw himself at him and kiss him.

“Alright baby boy, watch out”

With his two last shots, he hits the target right in the middle, under the really impressed stare of the showman.

“We'll take the biggest one” He says with an innocent smile.

The man gives it to them, a suspicious look on his face, but they’re gone before he can ask or do anything.

“What’s up with him?” Sam asks once they’re a few steps away

Dean puts one of his arm around his shoulder, a satisfied smile on his face.

“His gun has a bent site. Saw it the moment I picked it up”

“How did you win then?”

“I’m the best, ain’t I?”

“Kind of” Sam says, not letting his admiration show.

They walked toward the Great Wheel and got into one of the cars, sitting next to each other while making sure to leave some room for Sam’s teddy bear.

The wheel starts rolling, slowly lifting them from the ground until they can see the whole city, hundreds of lights illuminating it. The air is cold enough to give Sam a reason to slide into Dean’s arms, searching for a source of warmth.

“Thank you” He says after a while, “For tonight. It’s… It’s really nice. You didn’t have to”

“Of course I did. I rather be with you than with anyone else, you know that, right?”

“Yeah” He lies, not wanting to contradict Dean. He knows that isn’t true, that if a girl had showed up tonight and flirted with him, there’s a good chance that he would have gone with her.

He can’t count the number of times where it's happened, can’t say how many time he got left alone because someone was more interesting or more funny than him. He’s more of a burden to his brother than anything else, even though Dean tries to deny it.

“I wish I was in your head, sometimes” Dean says, “Just so I could tell you how stupid you are for believing any of the things you’re telling yourself”

“Not telling myself anything”

“Yes you are. I can see it. And I can tell you that none of them are true” He pulls Sam closer to his chest, until his head is completely resting on it, and Sam takes a big breath, enjoying his brother’s scent. “The fact that Josh is an asshole has nothing to do with you. I know plenty of men who would throw themselves at your feet”

“That’s not true”

“Yes, it is” Dean hurries to say, “I know you can’t see it, but you’re… You’re perfect, Sammy. You’re funny, you’re smart, you’re interesting, you’re hot as fuck. If you weren’t my brother, I would do you immediately”

“Ew, Dean” Sam laughs, trying to cover how the blush that is spreading on his face. Does Dean really mean it? Or is he only saying it to be nice?

“What? We would be a cute couple”

“You’re into boys now?”

“I would make an exception for you. Always making an exception for you”

Sam doesn’t answer, choosing instead to lay still on Dean’s chest, listening to the way Dean’s heart beat, rocking him slowly.

Sometimes, he wonders if Dean is feeling the same way. If maybe this dark thing isn’t only on him, but on both of them, something that they create together without even being aware of it.

But he doesn’t want Dean to feel like he feels. Doesn’t want him to feel trapped, to feel alone and sick, so fucking sick, to feel like he doesn’t belong anywhere, like he doesn’t deserve anything good. He doesn’t want him to feel like he’ll never be happy, not completely, because a part of his soul is missing.

“Come on, it’s time to go” Dean says, taking Sam out of his thoughts.

A little dizzy, Sam gets up and follows Dean, letting his body fall a little against him. They’ve been here for a few hours now, but all the emotions are exhausting and he really wants to lay down for a while.

“I was thinking we go back to the motel, and watch a movie? I bought something that you should like”

“Yeah, it’s-“ Sam cuts himself when he recognizes Josh in front of them.

Josh, with three of his friends and their girlfriends, a girl holding his hand while he kisses her lips shyly.

It’s like a stab in the heart.

Is this why Josh left him? For a girl? What does she have that Sam doesn’t? Is this new? Or has Josh been playing with him since the beginning?

They never went out together at school, because Josh said he rather them be discreet, choosing to only tell it to his closest friends. So much for discretion.

“What?” Dean says when he notices the weird look on Sam’s face

“Nothing. Let’s go home”

“I can see that something is wrong” Dean turns around, and much to Sam's dismay, he spots Josh right away, “Tell me I’m dreaming”

“It’s ok De”

“Ok? No, it’s not fucking ok! This fucker broke up with you this morning, and he’s already out with a girl!”

“Yeah well, nothing I can do about it” Sam says, pushing his hands in his pocket as best as he can without dropping his giant teddy bear. He’s feeling so humiliated. So stupid. How could he not see that Josh was into someone else? He can’t even imagine how much Josh and his friends must have laughed, hearing Sam planning their Valentine’s date while they all knew it wasn’t gonna happen.

“Does he know me?”

“What?”

“Me. I’ve seen him plenty of times, but he never saw me, did he?”

“No?” Sam says, confused

“Good”

That’s the last thing Dean says before cupping Sam’s face with his hands and pushing his lips against his. He’s too taken to do anything at first, simply stand here while Dean’s lips are moving against his.

What is happening? Why is Dean doing that? Did he die earlier and is now living in heaven?

He stops thinking completely when he feels Dean’s tongue pressing against his lips, asking for entrance. He opens his mouth slowly, letting his brother slide inside, and slowly, he finally closes his eyes, savoring the moment.

Dean’s hands move from his head to his waist, one of his legs going between his, Sam’s hardening dick resting on it, and it would have been awkward if it wasn’t for the fact that Sam can feel Dean’s own boner against him.

“Shit” He whispers, rubbing his cock against Dean as best as he can while deepening the kiss.

“Sam?” Someone calls behind him

They painfully stop kissing, their bodies screaming at them to get back together, and Sam turns around to face Josh, his new girlfriend, and some of his friends.

He can see the hurt on Josh’s face, the realization that he wasn’t that special to Sam, after all, and Sam isn’t ashamed to say that his dick twists at this sign.

“Hey Miranda” He says with a fake smile, “How are you?”

“Good, I, uh” She turns her attention toward Dean, her most beautiful smile on display, “I’m sorry, I don’t think I've seen you at our school. Are you new?”

“Oh sorry, I didn’t even introduce myself” Dean says, pushing one of his hands inside Sam’s back pocket giving his ass a firm squeeze, “I’m Dean, Sam’s boyfriend. I’m a Sophomore in college so that’s probably why you've never seen me”

“College?” Miranda repeats, her eyes shinning with admiration and a hint of jealousy. How could she not be jealous? Sam is dating a hot, sexy, perfect college student, while she’s out with _Josh_ , who still has his mom preparing his lunch every morning.

“Yeah” Dean laughs, “Well, sorry to cut this short but Sammy and I have… Things, to do. Have a great night”

“You too, Dean” She replies, giggling a little as she does so, “See you Monday Sam!”

There’s no doubt in Sam’s mind that he’ll have to submit himself to an interrogation Monday, but he doesn’t care, not when he can feel Dean’s fingers rubbing his ass gently, sending waves of shivering through his whole body.

“So college, huh?” He asks as they start walking to the car

“Yeah, I’m actually majoring in biology”

“Really? Is there a chance you would give me a… private class? I really need help”

“Ah well, I can’t say no, can I? But there will be a price, you know”

Sam laughs softly as Dean pushes him against the car, his legs spreading to give him some room. Dean’s face is only a few inches away from his, his breath hitting his skin every time Dean’s chest raises, making Sam shiver in pleasure and want.

“Wouldn’t expect it any other way”

This time, it’s Dean’s turn to laugh before pressing his lips to Sam’s again. But he doesn’t have to wait before Sam opens his mouth, ready to welcome him.

There are a lot of things he needs to ask, to know, but right now, all he can think about is knowing if the lube and condoms from earlier are still in the car.

 

[](https://ibb.co/g7nkDv9)

 


End file.
